Tetrahydrofuran → 3-Cyclohexyl-6-[2-methoxy-4-(2-oxo-1,3-oxazolidin-3-yl)phenyl]-1-methyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

HRID 915959

反応式

HRID 915959 の反応式
O1CCCC1.[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[NH:14][C:15](=[O:29])[C:16]3[C:21]([CH:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)=[N:20][N:19]([CH3:28])[C:17]=3[N:18]=2)=[C:9]([O:30][CH3:31])[CH:8]=1.Cl[C:33]([O:35][CH2:36][CH2:37]Cl)=[O:34].C(=O)([O-])O.[Na+]>C(N(CC)CC)C>[CH:22]1([C:21]2[C:16]3[C:15](=[O:29])[NH:14][C:13]([C:10]4[CH:11]=[CH:12][C:7]([N:6]5[CH2:37][CH2:36][O:35][C:33]5=[O:34])=[CH:8][C:9]=4[O:30][CH3:31])=[N:18][C:17]=3[N:19]([CH3:28])[N:20]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 123052-Chloroethyl chloroformate2 回HCID 516892Sodium BicarbonateHCID 1359488876-(4-Amino-2-methoxyphenyl)-3-cyclohexyl-1-methyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

生成物 1

HCID 1360058733-Cyclohexyl-6-[2-methoxy-4-(2-oxo-1,3-oxazolidin-3-yl)phenyl]-1-methyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one収率 65%

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒

実験手順

To a 6 ml tetrahydrofuran solution of 150 mg (0.425 mmol) of the compound obtained in Example 44, 79 μl (0.765 mmol) of 2-chloroethyl chloroformate and triethylamine were added, and the mixture was stirred at room temperature for 20 hours. Further, 30 μl (0.29 mmol) of 2-chloroethyl chloroformate was added, and the mixture was stirred at room temperature for 4 hours. Then, an aqueous solution of sodium hydrogen carbonate was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with water and a saturated aqueous solution of sodium chloride. After the washed layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. To a 2 ml ethanol solution of the residue, 1 ml of a 1M aqueous solution of sodium hydroxide was added, and the mixture was stirred at room temperature for 5 hours. Then, the reaction mixture was neutralized with a 1M aqueous solution of hydrochloric acid, and extracted with chloroform. The organic layer was washed with water and a saturated aqueous solution of sodium chloride. After the washed layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was recrystallized from ethanol to obtain 116 mg (65%) of the captioned compound.

後処理

  1. stirringthe mixture was stirred at room temperature for 4 hours
  2. extractionthe mixture was extracted with chloroform
  3. washThe organic layer was washed with water
  4. dry with materialAfter the washed layer was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. additionTo a 2 ml ethanol solution of the residue, 1 ml of a 1M aqueous solution of sodium hydroxide was added
  7. stirringthe mixture was stirred at room temperature for 5 hours
  8. extractionextracted with chloroform
  9. washThe organic layer was washed with water
  10. dry with materialAfter the washed layer was dried over anhydrous sodium sulfate
  11. distillationthe solvent was distilled off under reduced pressure
  12. customThe residue was recrystallized from ethanol

出典と根拠

ORDレコード
ord-87c775a0fec840318451c5ca000e20f9
出典データセット
uspto-grants-2007_09
特許番号
US07268128B2

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